First time raw, planned or unplanned?

[Guest Upstateguy518]

Definitely planned. I went to his place looking to get fucked. He was married and didn't have condoms as his wife was older and they didn't need them. I actually thought about driving away when I pulled up but decided to man up and do it.

He was already hard with some lube at the ready for me. After a few minutes, He pushed inside me and I really didn't feel much difference between raw/condom. It was exciting though taking my first raw cock.

Sadly, it didn't last long. His promise to pull out wasn't one I expected him to keep and he didn't. He even claimed that he came on my back and not in my ass but the cum I pushed out into his toilet said otherwise. I didn't say anything to him until i got home and i actually ended up thanking him. I haven't bottomed raw since but I am very open to doing it again.

[BareboyQ]

My first time taking a cock up my ass was bare. I met up with that hot guy and also took condoms with me. We were making out and getting naked. Then i saw his huge cock, not only long but also had a big girth. I sucked him as good as possible and enjoyed his precum oozing out like crazy. I pulled out the condoms but he said they won't fit him and he doesn't have any that would. Guess he just wanted to breed my virgin hole but I agreed. It really hurt when he shoved his monster inside me and he wasn't gentle then neither. He pushed me against the wall, the bed or whatever he felt like to prevent me from escaping his huge cock and the heavy thrusting. I started enjoying it more and more and after an hour or so he started pumping a huge load if his seed inside me.

I spend the whole afternoon with him and he bred me a couple of times and i tried to keep as much inside me while u.was driving back home in the train later.

So it was unplanned but i loved it.

[cumslutfuckpig]

First time was in the early 90s right after I came out.  Somehow I landed this gorgeous, hung muscle daddy who liked to call the shots.  The first time we got together we were rolling around together and his cock was rubbing against my hole which felt great - and naughty.  Then he put his 80-lb weight advantage to use and stared me down.  I thought, he’s playing, but to my shock he kept pushing into the nuts, never losing eye contact, daring me to tell him no. He fucked me sideways, and during the times we played I never told him no ... and he never came in me.  Before he moved, he was telling me no (to breeding).  

[Guest]

Unplanned! My first time was around 18. I was of the mindset ‘I’ll only ever use condoms’. Strict, no way around that.

 

While I lived with my parents I’d spend most nights at my buddies place - 40’s hairy bald bear guy. He was my first time topping as I had mostly only done oral and we tried used a condom. Every time I wasn’t able to stay hard, so he’d blow me and we’d cuddle.

 

After this three or so times, we had finished and were all lubed up swinging in a hammock. I was spooning him, hard as diamonds and half asleep. While I don’t remember exactly how, my cock ended up raw inside him and I froze. “I don’t have a condom on”, to which he responded “it’s ok”.

 

Cue the next couple months before heading off to college I’d breed his hole several times a day (luxury of being young and horny).

 

Turns out he was a total raw pig - he had a huge fetish for younger ‘condom to bareback’ that I’m not even sure he knew. Loved being surprised by condom removal and all that.

 

After him I really never went back. Impossible to, in my opinion.

[Guest Porthos]

My first time raw was also the first time I ever fucked...It was the late 90's and there was a plaza where late at night was a big cruising spot for cars. I'd go there often, meet up with another guy and we would usually go to a more private location where we could meet up. It was always oral...Really hot guys I would make out and kiss but it always ended up with just blow jobs. Then one night I met a guy a little older than me..thin, tall, sandy hair. He drove a big american car with a bench seat. I got in the passenger side ans we started making out, then sucking each other off. He was giving me a nice wet sloppy blow job when all of a sudden he sat up and moved over to my side, facing me and started to guide my wet cock to his hole. He slid down balls deep and then began bouncing on my dick...The feeling was incredible and within less than a minute I lost control and shot  a huge load.  I literally came without warning.  I was out of breath and my heart beating furiously. He slid off and a huge glob fell in my pubes. I was now freaking...not mad at him but now worried about condomless sex....This was at the height of AIDS.

I went home and obcessed for days but got over it quick....The next year I had a bf...we never used condoms

[Piggyybttmm]

First time raw I was stealthed. I didn't know he took off the condom till he busted in my ass. But I never looked back

[chargedodger]

On 3/29/2020 at 8:14 AM, DannyBoyCMH said:

I was raped when I was young.  So... unplanned.

Me too.Scared but excited too.

[norcalraw]

It was not even in my consciousness that I was going to get fucked the first time I got with a man, and that it was going to be raw.  I was 19, he was 35, invited me to his place after we finished a mutual business conference.  He had a great place and hot roommates. We went to go sit and relax in his hot tub, I didn’t have swim trunks so I stripped and went naked. Was immediately hard as I was embarrassed and entered tub. I wasn’t sure what I was doing, I knew I was into men, but wasn’t sure that’s what this guy was into. As turns out he was totally horned up and was right on me kissing, fingering my hole, stroking my cock. He started breeding me in the tub. We then moved to his room and continued fucking me there. I had so much cum running down my ass and leg. Only regret that night, was that his sexy roommates didn’t join in.  Obviously no condom was used, wasn’t even an option the way he went after my ass. He needed to breed me, I needed cum and to learn how to be a good cumhole for men. 

[Bibttmmiami]

On 8/9/2017 at 7:16 AM, Guest Lempriere said:

Have you taken his load since then?  Very hot.  Would love to hear more.

No. That was actually the last time we ever hooked up. 

[Guest]

I’d say planned, I always had sex with condoms until I got an urge to be bred by a much older top, when I finally managed to arrange a meet up with Liam (who is now my partner, totally bb partner) there was no mention of a condom or any form of protection, I sucked his cock, got on my hands and knees and he shoved it in, I didn’t stop him or ask for him to pull out, he’d said when we were chatting that when he fucks he always cums deep! 
I guess it was totally planned 😈

[ijoey]

First time fucked was raw and was mostly unplanned, but I knew if I went back to his house. His intention was to fuck me

I wasn't wrong

Within 5 minutes, I was naked on his bed. He reminded that from day 1 he was going to fuck me and fuck me raw. I nodded and he ate my sweet hole.

I was soon begging for his 8inch cock to breed my married hole. It took him forever to get it all inside me, but he finally did and he stayed there all weekend (wife was out of town). I went back very often

[cumbro]

Unplanned. Craigslist hookup in LA. A really hot latino jock said he wanted to get fucked. But within minutes, he had flipped me onto my stomach, pinned me, and fucked me hard. No condom, and I definitely freaked out having always played safe. But it felt so incredibly wonderful, and he was totally hot, telling me he knew I wanted it. I had no idea what I’d been missing. That was ten years ago, and I still jack off thinking about him.

[Throwaway325]

Unplanned 100%. I was chatting with a guy online and we met up for a drink. We were both totally into each other and soon would up making out in my car. Drove around a little playing with each other in the car and finding a secluded area. 
Finally we parked in a little lot hidden by trees and kept fooling around. I was only planning on some oral/jo type okay but before I knew it he was sucking my dick telling me how bad he wanted it in him. 
Totally unplanned and with only spit and determination I was balls deep in him.  It was years ago and I never saw him again but definitely the first time I’d ever felt skin on skin and I got addicted haha

[shinelover]

My first time raw was unplanned. It was late at night, I'd been drinking earlier and was horny as hell. Connected with a guy on Squirt and he was at the door within ten minutes.

I'd been using various toys on my ass for hours so I was already lubed and open. Before he arrived I'd put out some lube, towels, and condoms. Now that I think about it, even then I'd had a feeling he wouldn't be using the condoms that night. And he didn't ask and I never said anything.

[paintedgrey]

Unplanned, but then so was the whole event.  Went round a friends house to do some work for him.  He suggested we went to the bedroom, which we did.  We got naked and made out, then leaned over to the side of the bed to grab a condom, he looked at me and just said 'we don't need one of those do we', and put it back on the side.  He held my legs up on his shoulders and fucked me hard, he was about to cum when he pulled out and said "i'm going to cum, is it alright?" I nodded, said yes please, and he slid back in, seconds later giving me his load. Good memories.